A lake surrounded by autumn-colored trees reflecting on the water.

Search Middletown Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Middletown cottages

A rustic cabin with a stone exterior, wooden deck, and a small porch.

1. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$328 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
Hello Small Stone
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$283 nightly
The price is $295
Nov 1 - Nov 2
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$304 nightly
The price is $344
Oct 27 - Oct 28
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

4. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
$192 nightly
The price is $216
Oct 27 - Oct 28
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

5. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
$252 nightly
The price is $256
Nov 12 - Nov 13
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

6. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
$461 nightly
The price is $545
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A wooden deck with a white railing, surrounded by a grassy lawn and trees.

7. Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.2 out of 10, Wonderful, (5 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$426 nightly
The price is $481
Oct 27 - Oct 28
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Exterior

8. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$376 nightly
The price is $414
Nov 2 - Nov 3
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
A covered patio with wicker furniture, a fire pit, and a view of a grassy area.

9. Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
$800 nightly
The price is $891
Nov 3 - Nov 4
Total with taxes and fees
Lakefront | Sport Courts | HotTub | GameRoom
A house with a view of a bridge and mountains.

10. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (149 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Oct 28 - Oct 29
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

11. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
$457 nightly
The price is $517
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

12. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
$591 nightly
The price is $698
Nov 22 - Nov 23
Total with taxes and fees
Bright Cornwall-on-hudson Vacation Rental!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"I took my daughter here for her birthday weekend last week and she had a blast!! The resort has everything a six year old would want. Food, ice cream, plenty of games and the water park was fun. Pretty nice bar downstairs in the main lobby and inside the water park for us adults. Drinks cost what you’d expect at a water park resort about $12-15 on average ."
Anton L 1-night trip
Posted 8 hours ago
The Kartrite Resort & Indoor Waterpark

Find out more about Middletown

Middletown Cottages information

Number of reviews
238
Accommodation
140 Cottages
Lowest Price
$216
Highest Price
$891

Frequently asked questions

Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodations that'll make your wallet smile, narrow down your search by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

Explore a world of travel with Expedia